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Valacyclovir hydrochloride

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Valacyclovir hydrochloride Basic information

Product Name:
Valacyclovir hydrochloride
Synonyms:
  • 2-[(2-azanyl-6-oxo-3H-purin-9-yl)methoxy]ethyl (2S)-2-azanyl-3-methyl-butanoate hydrochloride
  • L-Valacyclovir Hydrochloride
  • Valacyclovir Hydrochloride (200 mg)
  • L-Valine, 2-[(2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy]ethyl ester, monohydrochloride (9CI)
  • Valtrex
  • VALACYCLOVIR HYDROCHLORIDE [9-((2-HYDROXY-ETHOXY)MET HYL)GUANINE L-VALINE ESTER HYDROCHLORIDE]
  • (S)-2-((2-AMINO-6-OXO-1H-PURIN-9(6H)-YL)METHOXY)ETHYL 2-AMINO-3-METHYLBUTANOATE HYDROCHLORIDE
  • 9-((2-Hydroxy-ethoxy)methyl)guanine L-valine ester hydrochloride
CAS:
124832-27-5
MF:
C13H20N6O4.ClH
MW:
360.8
EINECS:
641-092-8
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  • Valacyclovir
Mol File:
124832-27-5.mol
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Valacyclovir hydrochloride Chemical Properties

Melting point:
170-172°C
storage temp. 
Keep in dark place,Sealed in dry,Store in freezer, under -20°C
solubility 
H2O: >20mg/mL
form 
solid
color 
white
λmax
253nm(H2O)(lit.)
Merck 
14,9899
Stability:
Hygroscopic
CAS DataBase Reference
124832-27-5(CAS DataBase Reference)
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Safety Information

Hazard Codes 
Xi,Xn
Risk Statements 
36/37/38-22
Safety Statements 
26-36-24/25
RIDADR 
3077
WGK Germany 
3
HS Code 
29335990
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Valacyclovir hydrochloride Usage And Synthesis

Description

Valacyclovir hydrochloride, an orally active L-valyl ester of the potent antiviral agent aciclovir, was launched in 1995 in the United Kingdom for the treatment of herpes simplex virus (HSV) infections of the skin and mucous membranes, including initial and recurrent genital herpes. As a prodrug, valaciclovir has an improved pharmacokinetic profile to aciclovir. It is rapidly absorbed after oral administration and extensively converted to aciclovir via first-pass metabolism to achieve plasma levels of aciclovir comparable to those seen with aciclovir via i.v. route. Valacyclovir is then activated selectively in virus-infected cells by viral thymidine kinase to form aciclovir triphosphate in a stepwise fashion. This active species inhibits viral DNA polymerase via irreversible binding to the active site of the enzyme. Once aciclovir is incorporated into the elongating viral DNA, it terminates replication of the viral DNA strand, an antiviral mechanism unique to aciclovir. Valacyclovir is reportedly in clinical trials for the suppression of cytomegalovirus infection and disease in renal transplant patients.

Chemical Properties

White Crystalline Powder

Originator

Glaxo Wellcome (United Kingdom)

Uses

Acyclovir (A192400) impurity. The L-Valine ester prodrug of Acyclovir.

Uses

Valaciclovir hydrochloride is an antiviral drug used in the management of herpes simplex, herpes zoster, and herpes B.

Definition

ChEBI: Valacyclovir hydrochloride is an organic molecular entity.

brand name

Valtrex (GlaxoSmithKline).

General Description

Valacyclovir (Valtrex) is the hydrochloride salt of the Lvalylester of acyclovir. The compound is a water-solublecrystalline solid, and it is a prodrug intended to increase thebioavailability of acyclovir by increasing lipophilicity.Valacyclovir is hydrolyzed rapidly and almost completely toacyclovir following oral administration.
Valacyclovir has been approved for the treatment of herpeszoster (shingles) in immunocompromised patients. Theside effect profile observed in valacyclovir is comparablewith bioequivalent doses of acyclovir.

Pharmacokinetics

The binding of valacyclovir to human plasma proteins ranges between 13.5 to 17.9%. The plasma elimination half-life of acyclovir is 2.5 to 3.3 hours. The bioavailability of valacyclovir hydrochloride is 54%, compared to approximately 20% for oral acyclovir, and it is as effective as acyclovir in decreasing the duration of pain associated with posttherapeutic neuralgia and episodes of genital lesion healing.

Side effects

The adverse effects are similar to acyclovir, which include nausea, headache, vomiting, constipation, and anorexia.

Valacyclovir hydrochlorideSupplier

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